
Here are my current plans:
Day 1 — overnight train from Saint Petersburg
Day 2 — overnight train from Saint Petersburg
Day 3 — Vladikavkaz
Day 4 — Tbilisi
Day 5 — Tbilisi
Day 6 — Gori
Day 7 — Kutaisi
Day 8 — Sukhumi
Day 9 — Sukhumi
Day 10 — Gagra
Day 11 — Gagra
Day 12 — Gagra
Day 13 — Sochi, flight to Saint Petersburg
Is this too ambitious? I certainly do not want to be on a bus all day without enough time to actually visit the different places, but from my initial research, the furthest drive (apart from the train journey, of course) would only be the 3.5 hours from Kutaisi to Sukhumi. And am I budgeting my time in the best manner? Before I make any final decisions, I am also considering staying within Russia and visiting the North Caucasus. I would be aiming to spend a good part of that time in Dagestan, primarily Makhachkala and Derbent. Is there anyone here who has been to both these regions and can offer a comparison? For some background information, I am an experienced traveller (so not interested in highly touristy sites) with some knowledge of Russian. I'm also doing postgraduate work in Eurasian Studies with particular focus on the Caucasus and Central Asia, hence I am determined to visit the Caucasus whether it's the North or South part!

Any advice is much appreciated!